I'm not sure this matters for anyone but just so you know some recent changes to the Win32 Squeak VM for making it fully Unicode aware have broken the support for Win95 and Win98. Since I am not planning to spend any time whatsoever on supporting these versions any longer[*1], you will have to use older (pre-3.10.x) VMs in order to run on these Windows versions. I recommend the 3.7.x series which was a particularly stable vintage ;-)
If anyone is interested in supporting Win95/Win98 specifically, drop me a note and we can work something out (maybe a branch on SqueakVM.org).
Cheers, - Andreas
[*1] Actually I may spend some time getting rid of all the crude workarounds that were necessary to support Win95 in the first place.